US5459245A - Fluorotriazine containing naphthylazonaphthyl monoazo reactive dyes - Google Patents

Fluorotriazine containing naphthylazonaphthyl monoazo reactive dyes Download PDF

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Publication number
US5459245A
US5459245A US08/330,230 US33023094A US5459245A US 5459245 A US5459245 A US 5459245A US 33023094 A US33023094 A US 33023094A US 5459245 A US5459245 A US 5459245A
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US08/330,230
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English (en)
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Horst Jaeger
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Bayer AG
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Bayer AG
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
    • C09B62/4401—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system
    • C09B62/4403—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring with two or more reactive groups at least one of them being directly attached to a heterocyclic system and at least one of them being directly attached to a non-heterocyclic system the heterocyclic system being a triazine ring
    • C09B62/4411—Azo dyes
    • C09B62/4413—Non-metallized monoazo dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/02—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring
    • C09B62/04—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group directly attached to a heterocyclic ring to a triazine ring
    • C09B62/08—Azo dyes
    • C09B62/085—Monoazo dyes

Definitions

  • the present invention relates to new reactive dyestuffs, a process for their preparation and their use.
  • the present invention relates to reactive dyestuffs which, in the form of the free acid, have the following formula ##STR2## in which R is hydrogen or sulpho,
  • A is a substituted or unsubstituted amino group, in particular one of the formula ##STR3## in which R 1 represents hydrogen or an aliphatic, cycloaliphatic or araliphatic radical and
  • R 2 represents R 1 or a heteroaryl radical or an aromatic radical, it being possible for the radicals R 1 and R 2 with or without inclusion of a heteroatom to form a ring.
  • heteroatoms for the ring formation of R 2 and R 1 are preferably O, NH, NCH 3 , NCOCH 3 , N--C 2 H 4 SO 2 CH ⁇ CH 2 , S,SO,SO 2 .
  • Preferred heteroaryl radicals R 2 and R 1 are 3-aminosulpholane, 2-aminothiazole, 6-amino-2-ethylsulphonyl- benzothiazole.
  • --NR 1 R 2 represents the radical of an aliphatic amine or of a heterocyclic amine in which R 1 and R 2 together with the joint N atom form a ring.
  • the aliphatic radicals represented by R 1 and R 2 are preferably alkyl radicals, in particular those having 1 to 6 C atoms, which may be interrupted by heteroatoms and are substituted or unsubstituted.
  • interrupting heteroatoms are:
  • O, S, SO 2 (is hydrogen, C 1 -C 4 -alkyl), NR 3 CO, NR 3 SO 2 ;
  • Z represents a heterocyclic reactive group, in particular one from the monochloro- and monofluorotriazine series or fluoropyrimidine series.
  • the cycloaliphatic radicals R 1 are in particular 5- or 6-membered cycloalkyl radicals.
  • the araliphatic radicals R 1 are in particular those of the formula ##STR4## in which n is 1 to 4 and the radical A can be substituted, for example by Cl, NO 2 , COOH, SO 3 H, CH 3 , OCH 3 , SO 2 CH 2 CH 2 OSO 3 H, SO 2 CH ⁇ CH 2 , CH 2 SO 2 CH 2 CH 2 OSO 3 H.
  • Aromatic radicals R 2 are in particular phenyl or naphthyl radicals which are unsubstituted or substituted, in particular by OCH 3 , OC 2 H 5 , OCH 2 CH 2 OH, CH 3 , C 2 H 5 , --CH(CH 3 ) 2 , F, Cl, Br, COOH, SO 3 H, NO 2 , SO 2 CH 2 CH 2 OSO 3 H, SO 2 CH ⁇ CH 2 , CH 2 SO 2 CH 2 CH 2 SO 3 H, CH 2 SO 2 CH ⁇ CH 2 , NHZ, Z having the above-mentioned meaning.
  • R 1 or R 2 aliphatic radical are as follows:
  • cycloaliphatic radicals R 1 and R 2 are: ##STR6##
  • araliphatic radicals R 1 are:
  • R 1 and R 2 independently of one another, denote hydrogen, C 1 -C 4 -alkyl, which can be substituted by OCH 3 , OC 2 H 5 , COOH, OSO 3 H, SO 3 H, OCH 2 CH 2 SO 2 CH 2 OSO 3 H, OCH 2 CH 2 SO 2 CH ⁇ CH 2 , OCH 2 CH 2 SO 2 CH 2 CH 2 Cl, SO 2 CH 2 CH 2 OSO 3 H, SO 2 CH ⁇ CH 2 ; in a further preferred embodiment, R 1 denotes hydrogen or C 1 --C 4 -alkyl and R 2 denotes a phenyl radical, which can be substituted by Cl, OCH 3 , CH 3 , SO 3 H, NO 2 , COOH, CN, SO 2 CH 2 CH 2 OSO 3 H, SO 2 CH ⁇ CH 2 , CH 2 SO 2 CH 2 CH 2 OSO 3 H, CH 2 SO 2 CH ⁇ CH 2 .
  • A represents the radical of a ring-closed amine, in particular ##STR10##
  • the invention furthermore relates to a process for the preparation of the dyestuffs of the formula (1), which is characterised in that first 2-amino-5-hydroxynaphthalene-1,7-disulphonic acid is condensed with trifluorotriazine in a pH range from 2 to 6, in particular 3 to 5, and at temperatures of -5° to +20°, in particular at 0° to 5°, if appropriate in the presence of a buffer, to give a difluorotriazine compound, and subsequently a further fluorine atom is exchanged for an amine radical A and finally the resulting monofluoro compound is coupled with the diazo compound of an amine of the formula ##STR11## in a neutral range.
  • Suitable buffers are in particular the alkali metal salts of the fluorides or phosphates.
  • the reactive dyestuffs of the formula (1) can be isolated and processed to give useful, dry dyestuff preparations. Isolation preferably takes place at the lowest possible temperatures by salting out and filtration.
  • the filtered dyestuffs can be dried, if appropriate by addition of a buffer mixture, for example mono- and disodiumphosphate; preferably, drying takes place at temperatures which are not excessively high and under reduced pressure.
  • the dry preparations according to the invention can be prepared directly, i.e. without intermediate isolation of the dyestuffs, by spray-drying the entire preparation mixture.
  • the new dyestuffs are suitable for the dyeing and printing of hydroxyl- and amido-containing materials, in particular cellulose materials. They are distinguished by high reactivity and a high degree of fixation.
  • the dyeings or prints on cellulose materials obtainable using these dyestuffs are moreover distinguished by a high stability of their fibre to dyestuff bond and by excellent stability to oxidising agents, such as peroxide- or chlorine-containing detergents.
  • oxidising agents such as peroxide- or chlorine-containing detergents.
  • the ability of the hydrolysis products formed only to a small extent during dyeing or printing to be washed out is excellent.
  • the dyestuffs have good wet fastness properties.
  • the salts are in general obtained, in particular the alkali metal salts, such as sodium salts, potassium salts or lithium salts.
  • the weights given in the examples are those of the free acid.
  • the colour indicator numbers given in the examples refer to the Colour Index Hue Indication Chart (Indicator Numbers).
  • a diazo compound obtained in the usual manner by direct diazotisation of 30.3 g of 2-aminonaphthalene-1,5disulphonic acid is added to this suspension at 5° to 10° while simultaneously maintaining the pH at 7.0 to 7.5 by sprinkling in sodium bicarbonate.
  • the orange-coloured dyestuff powder is readily soluble in water and dyes cotton by one of the methods customary for reactive dyestuffs in brilliant orange shades (colour indicator number 5).
  • a diazo compound obtained in the usual manner by diazotisation of 30.3 g of 2-aminonaphthalene-1,5-disulphonic acid is added to the resulting solution of the reaction product of the formula ##STR15## at 5° to 10°, while simultaneously maintaining the pH at 7.0 to 7.5 by sprinkling in sodium bicarbonate. After coupling is complete, the dyestuff of the formula ##STR16## is salted out, filtered off with suction, dried and milled.
  • the orange-coloured dyestuff powder is readily soluble in water and dyes cotton by one of the methods customary for reactive dyestuffs in brilliant orange shades (colour indicator number 5).
  • the orange-coloured dyestuff powder is readily soluble in water and dyes cotton in brilliant orange shades (colour indicator number 5).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
US08/330,230 1992-02-27 1994-10-27 Fluorotriazine containing naphthylazonaphthyl monoazo reactive dyes Expired - Fee Related US5459245A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US08/330,230 US5459245A (en) 1992-02-27 1994-10-27 Fluorotriazine containing naphthylazonaphthyl monoazo reactive dyes

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE4206040.0 1992-02-27
DE4206040A DE4206040A1 (de) 1992-02-27 1992-02-27 Neue reaktivfarbstoffe
US1975193A 1993-02-18 1993-02-18
US08/330,230 US5459245A (en) 1992-02-27 1994-10-27 Fluorotriazine containing naphthylazonaphthyl monoazo reactive dyes

Publications (1)

Publication Number Publication Date
US5459245A true US5459245A (en) 1995-10-17

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US08/330,230 Expired - Fee Related US5459245A (en) 1992-02-27 1994-10-27 Fluorotriazine containing naphthylazonaphthyl monoazo reactive dyes

Country Status (4)

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US (1) US5459245A (fr)
EP (1) EP0557841B1 (fr)
JP (1) JPH0641453A (fr)
DE (2) DE4206040A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6124441A (en) * 1998-04-15 2000-09-26 Dystar Textilfarben Gmbh & Co. Deutschland Kg Monoaso compounds containing a fluoro-triazinyl group linked with a fiber-reactive group of the vinyl sulfone series via an ethyl-n-methyly-amino group, suitable as dyestuffs
CN104559320A (zh) * 2014-04-28 2015-04-29 无锡润新染料有限公司 一种复合活性艳橙染料组合物
CN106009769A (zh) * 2016-05-17 2016-10-12 黄山普米特新材料有限公司 活性橙及其合成方法

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4404341A1 (de) * 1994-02-11 1995-08-17 Hoechst Ag Wasserlösliche Azoverbindungen, Verfahren zu deren Herstellung und ihre Verwendung als Farbstoffe
KR100270403B1 (ko) * 1998-03-26 2000-12-01 김충섭 이반응기형 적색 반응성 염료
DE19821347A1 (de) * 1998-05-13 1999-11-18 Dystar Textilfarben Gmbh & Co Wasserlösliche halogentriazinhaltige Azoverbindungen, Verfahren zu deren Herstellung und ihre Verwendung als Farbstoffe
US9767041B2 (en) 2015-05-26 2017-09-19 Intel Corporation Managing sectored cache

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4115378A (en) * 1967-04-19 1978-09-19 Bayer Aktiengesellschaft Water soluble reactive axodyestuffs containing a fluorotriazinyl group attached via a nitrogen bridge to the dyestuff molecule
US4206306A (en) * 1967-04-19 1980-06-03 Bayer Aktiengesellschaft Reactive phthalocyanine dyestuffs containing a fluorotriazinyl group attached via a nitrogen bridge to the dyestuff molecule
EP0144766A2 (fr) * 1983-11-09 1985-06-19 Ciba-Geigy Ag Colorants réactifs, leur préparation et leur utilisation
EP0172790A2 (fr) * 1984-08-21 1986-02-26 Ciba-Geigy Ag Procédé pour la conversion continue de fluorure de cyanuryle avec des amines aromatiques contenant des groupes sulfo
EP0299315A2 (fr) * 1987-07-16 1989-01-18 Bayer Ag Colorants réactifs
EP0299967A1 (fr) * 1986-03-29 1989-01-25 BASF Lacke + Farben AG Laque aqueuse pigmentee a deux constituants pour revetir en une seule couche des films de finition et des bords sans fin

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3545462A1 (de) * 1985-12-20 1987-07-02 Bayer Ag Reaktivfarbstoffe

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4115378A (en) * 1967-04-19 1978-09-19 Bayer Aktiengesellschaft Water soluble reactive axodyestuffs containing a fluorotriazinyl group attached via a nitrogen bridge to the dyestuff molecule
US4206306A (en) * 1967-04-19 1980-06-03 Bayer Aktiengesellschaft Reactive phthalocyanine dyestuffs containing a fluorotriazinyl group attached via a nitrogen bridge to the dyestuff molecule
EP0144766A2 (fr) * 1983-11-09 1985-06-19 Ciba-Geigy Ag Colorants réactifs, leur préparation et leur utilisation
US4754023A (en) * 1983-11-09 1988-06-28 Ciba-Geigy Corporation Reactive dyestuffs comprising a triazine moiety and a vinylsulfonyl moiety both being linked by a substituted alkylene bridge member
EP0172790A2 (fr) * 1984-08-21 1986-02-26 Ciba-Geigy Ag Procédé pour la conversion continue de fluorure de cyanuryle avec des amines aromatiques contenant des groupes sulfo
US4740597A (en) * 1984-08-21 1988-04-26 Ciba-Geigy Corporation Process for the continuous reaction of cyanuric fluoride with sulfo-containing aromatic amines
EP0299967A1 (fr) * 1986-03-29 1989-01-25 BASF Lacke + Farben AG Laque aqueuse pigmentee a deux constituants pour revetir en une seule couche des films de finition et des bords sans fin
EP0299315A2 (fr) * 1987-07-16 1989-01-18 Bayer Ag Colorants réactifs
US4988803A (en) * 1987-07-16 1991-01-29 Bayer Aktiengesellschaft Fiber reactive azo dyes containing a morpholinyl-, piperazinyl- or piperidnyl- substituted flurotriazinyl radical

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Buckley, Chemical Abstracts, vol. 58, No. 14156a (1963). *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6124441A (en) * 1998-04-15 2000-09-26 Dystar Textilfarben Gmbh & Co. Deutschland Kg Monoaso compounds containing a fluoro-triazinyl group linked with a fiber-reactive group of the vinyl sulfone series via an ethyl-n-methyly-amino group, suitable as dyestuffs
CN104559320A (zh) * 2014-04-28 2015-04-29 无锡润新染料有限公司 一种复合活性艳橙染料组合物
CN106009769A (zh) * 2016-05-17 2016-10-12 黄山普米特新材料有限公司 活性橙及其合成方法

Also Published As

Publication number Publication date
EP0557841A2 (fr) 1993-09-01
EP0557841A3 (fr) 1994-01-26
DE4206040A1 (de) 1993-09-02
EP0557841B1 (fr) 2000-05-10
JPH0641453A (ja) 1994-02-15
DE59310030D1 (de) 2000-06-15

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